Mechanism of formation phthalimide

Phthalimides - Organic chemistry

This reaction is a two-step synthesis of primary aliphatic amines involving the N-alkylation of followed by acidic or basic hydrolysis of N-alkyl-phthalimides. The has been reported to be easily deprotonated by KOH or NaOH because of the two electron-withdrawing groups (i.e.,carbonyl), resulting in a good nucleophile; after the N-alkylation, the N-alkyl phthalimide can be decomposed to provide pure primary amines. This reaction is known as the Gabriel synthesis of primary amine. It is found that under basic conditions for the hydrolysis of N-alkyl phthalimide, the second step is the rate-limiting step. The hydrolysis has been modified by using hydrazine. The reaction is generally used for the synthesis of aliphatic primary amines.

The standard method for cleavage of the N-substituted phthalimide is with hydrazine hydrate, effective under milder conditions than acid or base hydrolysis. Other hydrazines and primary amines have also been successful, e.g. methylhydrazine or N,N-dimethylpropanediamine: Org. Synth. Coll., 9, 13, 16 (1998). Another technique involves borohydride reduction to the hydroxy amide, and liberation of the amine with acetic acid, with cyclization to phthalide: Tetrahedron Lett., 25, 2093 (1984). For suggested improvements to the cleavage conditions in the Gabriel synthesis, see: J. Org. Chem., 61, 8063 (1996). Review of the Gabriel reaction: Angew. Chem. Int. Ed., 7, 919 (1968).

N-alkylated phthalimides, made from potassium phthalimide, are used for the synthesis of primary amines (Gabriel synthesis) by the hydrolysis reaction.

Phthalimide is used as a precursor to anthranilic acid, ..

Moreover,our synthesis method of N-alkylphthalimides is superior to othermethods, since, as the starting material, we use phthalimide instead ofits potassiumsalt, which makes the synthesis procedure very simple and convenient.

of phthalimide will dissolve in a liter of boiling water

They are also useful compounds in the synthesis of primary amines and amino acids for the application in the field of medicine and biological research.

Search results for Phthalimide at Sigma-Aldrich ..

Melting points of all the compoundsare in good agreement with literature data.In conclusion, we have been developing a simple method for theN-alkylation of phthalimide that occurs under mild conditions, usinginexpensivereagents and a household microwave oven as the irradiation source.

N-(Hydroxymethyl)-phthalimide for synthesis | VWR

Frequently, the term of imide refers to the combined forms such as maleimides, phthalimides, and succinimides which are used as plastic modifiers to improve heat-resistant, antioxidant and antifoulant properties.

The NP was a self-assembled form of a phthalimide based conjugat

Theirradiation of the mixtures in a domestic microwave oven leads in a remarkableshort time (4-10~min.) to the desired N-alkylphthalimides.Microwave heating and its application in organic chemistry for the reactions in'dry'media is currently developed successfully, and in the past few years therehas been a tremendous interest in this area.

Recent

Phthalimide preparation from phthalic anhydride - …

Efficient synthesis of amides directly from esters and amines is achieved under mild, neutral conditions with the liberation of molecular hydrogen. Both primary and secondary amines can be utilized. This unprecedented, general, environmentally benign reaction is homogeneously catalyzed under neutral conditions by a dearomatized ruthenium−pincer PNN complex and proceeds in toluene under an inert atmosphere with a high turnover number (up to 1000). PNP analogues do not catalyze this transformation, underlining the crucial importance of the amine arm of the pincer ligand. A mechanism is proposed involving metal−ligand cooperation via aromatization−dearomatization of the pyridine moiety and hemilability of the amine arm.

Phthalimide For Synthesis | VWR

The Gabriel Synthesis of Primary Amines | Amine | Ester

The reaction is usuallyratherslow but can be conventionally speeded by the use of aprotic solvent such asDMF.In the present paper, we would like to report the remarkable fast synthesismethod of N-alkylphthalimides via alkylation of phthalimide in 'dry' mediaundermicrowave irradiation.

Reviews

“ The mixtures were adsorbed on potassiumcarbonate and irradiated in an open Erlenmeyer flask in a domestic microwaveoven for 4-10~min. The reaction of phthalimide with alkyl halides Since the shape and size of the reaction vessel are important factors for theheating of dielectrics in a microwave oven, the preferred reaction vessel is atall beaker with a loose cover of much larger capacity than the volume of thereaction mixture. ”